


The Date

by wisepuma23



Category: Supernatural
Genre: BUT NOT NSFW, Destiel Fluff, M/M, SLIGHT debriel but not really, bottom!Dean, but just slightly, it'll be clear in the next chapter
Language: English
Status: In-Progress
Published: 2014-12-18
Updated: 2015-05-07
Packaged: 2018-03-02 02:12:41
Rating: Teen And Up Audiences
Warnings: No Archive Warnings Apply
Chapters: 2
Words: 3,269
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/2795939
Author URL: https://archiveofourown.org/users/wisepuma23/pseuds/wisepuma23
Summary: <blockquote class="userstuff">
              <p>Gabriel loved his brother, he really really did. . But he was reaching his limit on suffering through Cassie’s disgusting cow eyes on a certain green eyed fellow college student.  Gabriel planned to ask Dean out, get Cassie soooo jealous that he swoops in and ‘ruins it’ quotation mark quotation mark. It was foolproof!</p><p>Only problem was, Dean was 100% straight as a ruler.</p>
            </blockquote>





	1. The (Fool Proof) Plan

**Author's Note:**

> There will be THREE parts total to this mini-ficlet.

Gabriel loved his brother, he really really did. But he was reaching his limit on suffering through Cassie’s disgusting cow eyes on a certain green eyed fellow college student. The prick’s name was Dean, he was way smarter than the usual grunt and they both shared Psychology 101, the only class that he and Cassie didn’t share.

He stared at the back of Dean’s beautifully crafted head, the man was attractive to say the least. However, he had a plan to finally get Cassie and Dean to knock some boots, run it like bunnies, and such the like. Gabriel was a great brother if he said so himself. Hooking up his little bro was the saintly thing to do.

Gabriel planned to ask Dean out, get Cassie soooo jealous that he swoops in and ‘ruins it’ quotation mark quotation mark. Then Dean would swoon into Cassie’s arms and go on a date instead with him instead of Gabriel. And presumably go into the sunset to find the nearest church to get married in, or fuck, either was good. 

It was foolproof!

Only problem was, Dean was 100% straight as a ruler.

Which is also another reason Gabriel is gonna ask Dean Winchester, womanzier and skirt chaser, out on a date. His gaydar is best known to Man, and there have been rumors that Dean already went out on a date with Aaron Bass. So he’s gonna ask him out and know once and for all to see if Dean is straight as a slinky. He’s gonna ask him out in the Cafeteria at Dean’s table, which is conveniently right next to Cassie’s table. 

Lunchtime finally rolled around, and he had already told Cassie what to do in the history lecture. He stood up from the table and sauntered over to the table next door as he took a large bite out of a Snickers bar. He could see out of the corner of his eyes that Cassie was watching him with large owlish blue eyes. Scaredy cat, if he had the balls to ask the guy sooner, Gabriel wouldn’t be doing this. 

"Hey idiot." Gabriel yelled out as he stood directly behind Dean’s chair, the conversations at the table stopping to witness the spectacle. 

"What?" Dean asked irritably as he turned around in his seat to glare at him icily.

"Haha, I said idiot and you looked." Gabriel teased as he pulled out the grin he knew was annoying as fuck.

Dean’s pretty jolly green eyes narrowed even further. 

"Will you go on a date with me, loser?" Gabriel asked bluntly as he took another large bite out of the candy. By this time, the entire cafeteria quieted down until a single pin could be heard if dropped. In the silence, Dean blinked quickly with a slight color to his cheeks that Gabriel wasn’t totally sure was due to anger. He watched Dean’s mouth open, already forming the word ‘No’ when he’s quickly pulled aside by his best friend, Charlie. They talk too fast for Gabriel to make out, but he uses it as an opportunity to gesture wildly to Cas to get his damn butt over here. Castiel shakes his head and hunches in his seat, probably too embarrassed to do anything. 

That.

Goddamn.

Coward!

“Yes.” a soft voice speaks up, causing Gabriel to whip around to look at Dean’s nervous face, before he repeats again the agreement with a louder voice.

"What?" Gabriel asks dumbly, he didn’t actually expect this to work. Fuck, he needed to come up with a second plan and quick, so he quickly recovered and plastered on a smile that he was sure that made him look like a dick.

"Pick me up at my dorm at seven on Friday night, don’t be late, jackass." Gabriel asks as he swaggers back to his chair next to Cas and lays lazily with his feet propped up on the table. Conversations start back up again and the chatter fills up the cafeteria once more like normal. Castiel fixes him with a withering glare, those baby blues coulda killed him if it could.

"You asked him out, how could you?" Castiel growled out in a dangerous voice.

"One, now we know he’s not 100% straight so you got more of a chance bro. Another thing, we gotta get you some balls for you to go out with Dean on Friday instead of me.” Gabriel tells him in a more serious tone, rarely his plans start involving him more than necessary. So he finishes his Snickers bar in another large bite, since what else can he do? Chocolate is a good classic for cheering him up.

"So now what, brother?" Castiel asks reluctantly.

"Plan B." Gabriel says with a dangerously mischievous smirk.


	2. The 'Yes'

**Summary for the Chapter:**

> “He said that I gotta find a boy to date, figure out this bisexuality thing, and experiment. The thing is, Charlie, that I don’t even know any guys that like _like_ me.” Dean admitted, flashes of other freshman guys passed before his eyes but not a single one of them seemed gay. Maybe he didn’t have a built in gaydar.
> 
> _Why did Dean say yes to Gabriel asking him out?_

Gabriel paced in the Novak household, why was Cassie taking so long? He needed to be _sexy_ ASAP if he needed any chance of seducing Dean right outta Gabriel’s hands. Finally the bedroom door opened to reveal Cassie in a dark blue blouse that matched the color of his eyes and the pair of slacks that he was sporting seem to make his ass pop. Damn, even Castiel has turned up the sex hair to 11, and was that _eyeliner_?

“Damn bro, if we weren’t related…”

“Please do not finish that sentence, Gabriel.” Castiel said annoyed, the Sex God look fizzled right before his eyes, and turned back into good ol’ mortal Cassie again.

“Haha, there is that guy with the stick up the butt, I hardly recognized him!” Gabriel heehawed with a painful but manly slap on his brother’s back. He could see his younger brother about to retort a undoubtedly a sassy reply but at that very moment, the front door of their apartment ringed. Gabriel’s eyebrows raised as he glanced at the clock in the small kitchen, it was seven on the _dot._

“Damn, he’s punctual.” Gabriel conceded before he slammed open the door with a wolfish grin to greet the sculpted man before him. Dean was wearing a nicely pressed green shirt with rolled up sleeves and black slacks as well, oh hell, even his hair was _combed_. Gabriel only grinned wider when Dean looked up and down at Gabriel’s thrown together appearance, he was just wearing a slept in shirt and jeans and no self care whatsoever.

“So.” Dean fumbled, “Wanna go eat or something?”

“Real smooth, Winchester.” Gabriel snickered. Dean down right glared so much that Gabriel entertained the thought maybe Dean was just doing this for a prank or forced into it. However when Cassie walked into view from behind him, it was like watching one of those Transformers change in live action. Gabriel blinked in surprise as he saw Dean’s shoulders go slack and a transfixed look came over him. He had to stop himself from rolling his eyes, so maybe Dean was gay for the _other_ devilishly handsome brother, and he was tempted to ask Dean to take his little bro on a date instead. Or even just throw Cassie right into Dean’s arms and slam the door.

“Are you sure you wanna go on a date with me?” Gabriel asked sincerely, and subtly moving out of the way so Dean could see Castiel more.

Dean startled out of whatever hypnosis he was in, and cleared his throat unconformably before gruffly saying “Let’s go.”

 

++++++

_A Day Earlier_

 

Aaron leaned down to kiss Dean that made him shiver down to his toes. They had met at the bar and it sorta escalated from there, Aaron was about to drop out of school in his senior year while Dean was just in his freshman’s. He gasped as hands ran down his flank and clutched at his sore ass. Aaron pulled away and Dean tried to chase the warmth and let out a small whine as Aaron went back to pulling up his pants. Aaron had a job at the local Gas-n-Sip which will keep him afloat until that job at the think tank will pull through.

“Do you really have to go?” Dean pouted, he wasn’t usually clingy like this in his past one night stands, but then again, his one night stands have all been women.

“You have been a _great_ lay, Dean, I mean it. I think you’re gonna be the last one I’m going to have for a while since I’m gonna be busy for a long time. Besides, I think it was about time I stop picking up freshmen from bars anyways, but I won’t forget you, Dean.” Aaron told him with a smile, as he leaned down to pick up the strewn shoes from all around Aaron’s bedroom. Aaron looked back at him, Dean’s hair pulled in every which way from manhandling and the bedsheets that laid sinfully low on Dean’s bruised hips.

Dean stuck out his rosy red lips in even more of a pout, he had feeling that if Dean put some effort into it, they could be a thing. Like a _real_ thing. Dean moved in such a way that the sheets fell even more from his hips, revealing more skin that were riddled of hickies. Dean didn’t hold back the grin of satisfaction when he saw Aaron’s pupils widen with thinly veiled arousal. His self control was really something to admire.

“I’m sorry Dean, I can’t do this right now. I don’t have the time for a….relationship. I know you’re one of those ‘questioning’ types and I just wanna say; go find a boy to date. Develop and grow, figure out things about your sexuality. It took me a while to accept it, it took me all four years here for me to be comfortable with it. Go break a few hearts, or get your heart broken, either way is okay.” Aaron advised him, and gently pushed him into the pillows to leave a searing kiss that made his nerves lit on fire.

“And hey, if you’re still single when you graduate or drop out, call me alright? We’ll give it a go, okay?” Aaron reassured him, his cool brown eyes staring into Dean’s own green eyes. It finally sunk in that it might be the last time he might see this whirlwind that shook his whole world in a single night, and he wouldn’t see him for years. In a fit of courage, he tangled his hands in Aaron’s soft curly looks and made damn sure to give him the best kiss of his life. Dean pulled away to witness Aaron’s dazzled look on his face, a conflicted look passed through his features, but then Aaron seemed to shake himself out of it.

“I won’t forget you either, Aaron.” Dean said dreamily. He wanted to smack himself in the head for being such a sap. _What happened to no chick flick moments_ , Dean wanted to ask himself, but Aaron only huffed in amusement. He finally finished buttoning up his shirt and put on his blue employee vest that had a stitched on name tag. He gave a final run through Dean’s hair that mussed it up even more, and a kiss on his forehead and left his dorm. Dean felt a strange emptiness as he saw the man walk out of his life, they’ve only known each for a night but he felt more than that.

 _Why was he such a sentimental sack of shit?_ Dean shook his head in disapproval, and quickly dressed up back in yesterday’s clothes and left Aaron’s dorm without looking back. The first thing Dean does after losing his gay virginity card would be go to one of his best friends since forever, Charlie Bradbury. It was actually a short twenty minute walk to her dorm from Aaron’s, and before he knew it, he was knocking on her door.

“Oh hey Dean! I was just watching some good ol’ The Office, wanna join?” Charlie said immediately when she opened the door.

“Uh, sure.” Dean said awkwardly, Charlie was the only person he trusted to go about this, since she was gay herself. Charlie’s eyes narrowed in suspicion as she stepped out of the way to lead Dean in. The two of them sat down, with a small wince from Dean, on Charlie’s lumpy old sofa but she didn’t press the play button on her remote just yet.

“Okay, spill.” Charlie said seriously as Dean gulped, telling her was fine in theory but it was proving to be difficult.

“I um……...lost mygayvirginitycard.” Dean confessed in a rush, his eyes locked on the frozen screen, not able to look her in the eyes.

“What? Repeat that again. _Slower_.” Charlie demanded, as she scooted closer until their knees were touching in a sign of support.

“I finally took it up the ass, okay? When you told me about this whole ‘bisexual’ thing, I went to the bar and I did it. I found a lay and I tried it out.” Dean explained in a slightly frustrated voice, sometimes he wish he could just transfer his thoughts telepathically to Charlie, it seemed way easier.

“Huh.”

“What?”

“I just thought it would be the other way around, I just pegged you as that sort of guy, but hey, life throws you surprises everyday.” Charlie teased, and Dean shoved her playfully, she was such an annoying best friend sometimes.

“Oh my god, just shut up!” Dean demanded as he put the other freshman into a headlock, giving her a well deserved noogie.

“Ahh! You know you love me!” Charlie squealed as she struggled in his arms, throwing her fists into his chest and arms. After a few minutes of rough housing, they finally settled down and tended to wounds against their ego. It wasn’t a clean fight but Dean just simply dubbed it as a way to keep fit and keep Charlie on her toes. After eating a nice and warm hot pocket or two, Dean got serious again as he thought about Aaron. He remembered his advice to find another boy and date him, and get his shit sorted out. However, that was easier said than done. Dean Winchester may be smooth around the skirts, but when it came to dudes, he practically tripped over his own feet. It was downright embarrassing.

“Hey Charlie, there were some stuff that Aaron said to me, so can I ask you some questions? I need to clear my head a bit.” Dean asked, all traces of humor in the past few minutes gone.

“Aaron, huh? Isn’t the senior that’s dropping out? Never mind, tell me what he said, I gotta know if I have to kick his ass or not.” Charlie said as she smacked her right fist into her palm, she was joking but it seemed to fall flat.

“He said that I gotta find a boy to date, figure out this bisexuality thing, and _experiment_. The thing is, Charlie, that I don’t even know any guys that like _like_ me.” Dean admitted, flashes of other freshman guys passed before his eyes but not a single one of them seemed gay. Maybe he didn’t have a built in gaydar.

“One, there’s Garth. Two, I don’t know if you’ve noticed but Benny stares at you lot at lunch, and he totally has a crush on you. Three, I’ve noticed you checking out that sweet boy’s ass that sits just one table over at lunch, I think his name is Castiel or something. And it isn’t exactly unrequited if you know what I’m saying, eh?” Charlie elbowed him gently in the chest, and Dean was stunned by her willingness to help.

“And hey, I think I have a better gaydar than you do, like come on.” Charlie jested, her eyebrows raised comedically.

“Yeah, I think it’s broken or something. You like me, right?” Dean said, teasing right on back.

“Ewwwww! You know I don’t like you like _that_! You’re like a brother to me and you know you got the wrong parts, bro.” Charlie shoved at him roughly, giggling like a crippled hyena. After  few moments, she gathered her composure back together while they watched The Office. Laughing loudly at the classic Jim and Dwight pranks and shook their heads amusedly at Michael’s ignorance. Later, he groaned loudly as Charlie snatched the remote quickly from the table and paused it on Dwight’s angry face, in the middle of a rant about Jim’s latest shenanigans.

“Dude, I was watching that!” Dean whined as he threw a piece of a hot pocket wrapper at her red hair in retaliation.

“Dean Winchester, I got a plan, it’s called Prowling For Dick. What do you think of the name?” Charlie snickered as she batted away more torn up wrappers thrown at her.

“So here’s my plan, let’s start with Garth, he seems totally nice and you can totally ask him out.” Charlie ordered like a general, her voice stern like she was sporting a crown and calling herself Queen of Moons.

“Ask him out?!” Dean spluttered.

“You heard me right.” Charlie said in a no nonsense voice.

“But how?” Dean whined, Charlie freaking _knew_ he was a bumbling idiot around attractive guys.

“Well obviously, you’re gonna get some guts and I’ll even sneak in a flask if I have to. You will ask Garth Fitzgerald at lunchtime, I’ll even make an excuse for you guys if you wanna talk alone or something.” Charlie winked lewdly. Dean shaked his head in defeat, this girl was stubborn as an ass, but he loved her so goddamn much.

“You’re forgetting one thing, Charlie.”

“What?”

“I blush like a goddamn school girl around guys, how the fuck am I gonna ask Garth out, I know the guy’s tame as a fly but those eyes, man.” Dean admitted with a slight rosy color to his freckled cheeks. He moved past the shame with admitting that Charlie that he was a sucker for handsome eyes, one look and he was swept off his feet. However, he promised to slit her throat if she told anybody else, adopted sister or not.

“Practice, Dean, practice.” Charlie said ominously with a mischievous twinkle in her eyes.

“On who?” Dean demanded, if Charlie was gonna say Sam, he would goddamn walk out, or maybe punch Charlie. Either was good.

“You know what? I’m changing my plan, you’re not gonna ask out anybody. I’m gonna ask a good friend of mine to ask _you_ out instead. Don’t you worry a thing, brother, I’m gonna land you on a date!” Charlie said brightly, the lines around her smile crinkling good-naturedly. Dean prodded her for answers, but she remained tight lipped about the entire affair. Dean was left with a sense of foreboding about the entire thing, who knows what the hell was gonna happen at lunch now? Dean was left unsettled but nonetheless, hid his unease by laughing along with Charlie while they watched The Office.

+++

It was finally lunchtime, and Dean was practically wringing his hands all morning since he was gonna get asked out by a guy. A guy! Dean kept in mind about what Charlie said about who had been checking out his perky little ass, well, that did nothing to keep him from nervously looking at them over his notebook. He hoped that he didn’t weird them out, especially Castiel, he had the look of that he could punch a dude’s lights out.

“Hey idiot.” a voice smirked from behind him, Dean’s face stilled as he recognized that smarmy voice from anywhere. He darted a look at Charlie’s intense look of focus at her burger, carefully picking it apart.

_Oh hell no._

_  
_

**Author's Note:**

> Leave kudos and a comment please!


End file.
